


The New Assistant

by smokesforsterek



Category: Teen Wolf (TV)
Genre: Alive Laura Hale, Getting Together, M/M, Office AU, assistant!stiles, boss!derek, slight miscommunication
Language: English
Status: Completed
Published: 2016-12-03
Updated: 2016-12-03
Packaged: 2018-09-06 02:26:04
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 11,130
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8731132
Author URL: https://archiveofourown.org/users/smokesforsterek/pseuds/smokesforsterek
Summary: “I don’t have an assistant,” Derek barks out as he looks back to the pile of reports he needs to get done. After the last kid that tried to be his assistant left in tears after the first day, he’s decided he didn’t want an assistant at all anymore.
“Well according to Ms. Hale, you do now. She hired me. I must say your sister is very scary-”
“I don’t need an assistant,” Derek barks out.
Or, the one where Laura hires Stiles to be Derek's assistant.





	

**Author's Note:**

  * For [promisingahurricane](https://archiveofourown.org/users/promisingahurricane/gifts).



> Prompt from [promising-a-hurricane](http://promising-a-hurricane.tumblr.com/):How about stressed boss derek and new employee stiles (who laura hired without asking der) based on this convo: D: “I’m not a man of many words, but when I snap my fingers like this *snap* you come running.” S: “Ah that’s perfect. I’m someone of many words, but I’ll make it easy for you: When I move my head like this *shakes it* it means I’m not coming.”
> 
> I legit do not know how this got so long, but here it is! This was originally for Sterek Week, but life (and the length of this omg) got in the way and it had to be drawn out. But eh, better late than never? 
> 
> This is half beta'd, so if there are any mistakes, let me know and I'll be happy to fix em. I have no plans at the moment to continue this au anymore than this. 
> 
> Hope y'all like it!

It’s early on a Monday morning, and no one is supposed to be in the office. So Derek is surprised when he hears the soft rhythm of knocks come from the door, even more surprised when he sees a figure through the frosted glass. 

“Come in?” Derek calls in question, looking away from the stack of reports on his desk, curious to see who the hell else is at the office at 6 in the morning. 

“Mr. Hale?” the voice asks as it peeks into his office. It’s a guy, he’s wearing glasses and his hair is spiked up in the front. He’s got an adorable upturned nose and from the other side of the room with the fluorescent lights on, Derek can see his cheeks are dotted with moles. 

“Who are you?” he’s never seen the kid before, how does he have access to the building?

“Oh, uh. Hi, I’m Stiles Stilinski. I’m your assistant,” he steps into his office and lets the glass door close behind him. He’s wearing a plaid shirt that is covered by a soft looking sweater and khakis. He looks professional enough for a fortune 500 company. 

“I don’t have an assistant,” Derek barks out as he looks back to the pile of reports he needs to get done. After the last kid that tried to be his assistant left in tears after the first day, he’s decided he didn’t want an assistant at all anymore.

“Well according to Ms. Hale, you do now. She hired me. I must say your sister is very scary-”

“I don’t need an assistant,” Derek barks out.

“Oh, well Ms. Hale hired me to help you out. So she obviously thinks you need one. I have strict instruction to not touch any of your files or anything. I’m just here to make sure you eat three meals a day, drink water every now and then, weed out your phone calls, and keep your schedule in check,” the guy explains and it seems like the kid memorized his job description. 

“I don’t need an assistant,” Derek insists again. 

It’s quiet for a moment, “Okay,” the kid- Stiles- finally breaks it, “well, I’m to report here every morning at 6 am, and I’m not to leave until you do. So if you need anything, I’ll be at my little desk outside your door; twiddling my thumbs and playing solitaire.” Stiles points to the door, one hand in his pocket, and turns on his heels.

“If you play solitaire I will fire you. I’m not a man of many words, but when I snap my fingers like this,” he snaps his fingers loudly, “you come running. Find something constructive to do,” Derek flips open a new folder with more reports. 

“Give me something to do and I will be happy to do it,” Stiles shrugs. 

“Go get coffee,” Derek grumbles, the coffee they buy in bulk sucks. “Not Starbucks,” he adds as Stiles turns away to go do as he’s told. 

“Then what am I supposed to get?” 

“Anything but Starbucks,” Derek says seriously without looking away from his report. 

“I meant like, what is your order,” Stiles says and Derek can hear the annoyance in his voice. 

“Black with one sugar.”

Stiles sighs and starts to leave the office. He stops at the door and looks back at Derek. 

“By the way, I’m someone of many words, but I’ll make it easy for you: When I move my head like this,” he shakes his head from side to side quickly, “it means I’m not coming.”

Stiles lets the door close behind him. The glass door and walls show Stiles walking to the desk that is apparently right outside Derek's office again now and grabs his coat to fight off the cold New York morning air. 

Derek rolls his eyes and continues on with his work. 

Half an hour later, a blue cardboard cup is sat on his desk. 

“Black coffee with two sugars. Threw in an extra one to apologize for the comment earlier,” Stiles says a smile on his face. 

“It’s fine.” 

Stiles stands there, looking at him then glancing at the cup. Derek supposes he’s waiting for a reward or something. 

“Where is this from?”

“My best friend and his wife own a bookstore down the street, they have a little coffee shop in there,” Stiles smiles, his hands behind his back. 

“They’re open at 6 am?”

“Oh man no. I was a barista there for a while before you hired me, I still have a key.” Stiles is still standing there, so Derek decides to take a sip. 

“This is... actually pretty good,” Derek admits. 

“Thank you. Yeah, I was the one who told Scott he needed a coffee shop to compete with Barnes and Noble. Bloos was totally my idea, my baby if you will. Scott’s shop wouldn’t be the same without it and -”

Derek interrupts, “go back to your desk. I have work to do.”

“Umm, yeah. Of course. Sorry to bother you sir,” Stiles turns and leaves the room. His voice lost all enthusiasm, it kind of makes Derek feel guilty. Nevermind, he has work he needs to do. 

A few hours later, the phone on his desk rings, he answers it without question as he does for every phone call. 

“Hale,” is all he says instead of an actual greeting. 

“It’s lunch time,” the voice on the other line says.

“I’m sorry?” Derek is confused, the voice isn’t familiar to him and it can’t possibly be noon. He’s only been working for a few hours, he looks at the clock on the wall to see that yes, it is indeed lunch time. 

“Lunch, Mr. Hale. I’m calling to ask you what you want for lunch,” the voice says, and Derek has no idea who it is. 

“Who is this?” 

“Stiles. Your assistant. We met this morning,” the phone sounds like it was put down. Then his office door opens and Stiles walks in, waves, says ‘hi’, then leaves. The phone gets picked up again. “I’m calling for your lunch order.”

“Ummm,” Derek has no idea. He wasn’t even hungry until he noticed the time, the idea of lunch sounds really good right now. “A salad?”

“Oh-kaaaay, anything specific?” 

“No.” The line goes quiet in awkwardness for a second. 

“Right. Well, I’m heading out now and I’ll be back in a bit.”

“Fine.” Derek hangs up the phone and goes back to his work. From his desk he can see Stiles’ figure get up and leave.

The realization that he was actually hungry annoyed him. Mostly because now his stomach was growling for food and every minute he went without food seemed like eternity. So when a shadow comes towards his door, he hopes it’s Stiles. The shadow puts a bag of what he hopes is food down on the desk outside and shrugs off a coat. 

It’s Stiles. 

A knock at the door confirms it, and Stiles lets himself in. 

“Here you go Mr. Bossman. A salad.” 

The black container with clear lid is set on his desk, a fork next to it along with a bottle of water. “Got you water because I figured you wouldn’t want a Coke with your salad,” he huffs out a laugh and puts his hands on his hips. His hands are veiny and sit on his slim hips just right. 

“Thank you,” Derek tries hard not to attack his lunch and instead waits the few seconds for it to become awkward enough for Stiles to leave. 

“Right, I’ll be outside. When you’re done, I’ll come collect your trash.” Stiles leaves. 

Okay, so maybe Laura had a point in hiring him another assistant, the convenience of having his food brought to him is nice. 

He eats the salad fast, he was pretty hungry after all, but he waits a while to call in Stiles to come get the trash. When he does, Stiles comes in holding another cup of coffee. 

“I want my lunch on my desk by noon from now on. This wasn’t very good so try somewhere else next time. I have a meeting in an hour and you need to come to take notes,” he looks at Stiles who has gathered the container and empty water bottle in his hands and put a coffee cup down on the desk.

“Yes, I was actually just about to remind you about your meeting with Mr. Argent,” Stiles says. 

“I don’t need reminding,” Derek grumbles as he takes a swig of his coffee. He idly wonders if there are two sugars in it again. 

“Well, you need someone to take notes, and that’s what I’m here for. If you need anything I’ll be outside gossiping.” 

Derek rolls his eyes as the kid leaves his office again, then like clockwork, forty-five minutes later, Stiles bursts in announcing they need to leave for the meeting. 

The meeting is boring and long, but Stiles sits on a chair in the corner and seems to be taking a transcript of the meeting. He’s writing fast, and doesn’t look up at all. 

After the meeting, Stiles says he’ll type up his notes and have them on Derek’s desk as soon as he’s done. It’s nearly three when Stiles plops down a ten page packet on his desk. 

“There’s the notes, I’m gonna make another coffee run, want one?” He doesn’t even seem phased by Derek’s surprise. 

“What the hell is this?” Derek lifts the packet to see it’s single spaced. 

“The notes,” Stiles says.

“I was in the meeting, I don’t need this many notes. Next time write less.” He tosses it in the trash, “Try again, and be more succinct. And yes, I want another coffee. One sugar.” Stiles huffs out a breath and leaves, grabbing his coat and leaving the office. 

A while later, Stiles puts the coffee down on his desk and leaves without a word. Derek watches him leave and Stiles’ frame is glorious. His assistant is totally his type, and he can’t help but wonder if Laura hired him for some other reason. 

He puts the thought out of his mind. Calls come in from Stiles announcing someone on the line for him, Derek calls for Stiles to run files over to Laura. The day goes on. 

The clock hits 7 pm and he realizes that the sun is going down. Stiles brought him dinner at 6, but he got lost in the focus group results instead of actually eating. 

He grabs the steak and eats it quickly. The water that is with it is much appreciated, he’ll need to tell Stiles to keep more water around. Laura was right, he doesn’t really take care of himself. 

He picks up the phone, “Stiles come in here,” and hangs up. Not even ten seconds later Stiles is pushing into his office, shirt rumpled and hair messy. Derek remembers that he’s been here as long as he has. 

“I need more water to be kept, buy a fridge and keep it stocked with water. Also, it’s late. You can leave if you need to.”

“I’m just supposed to buy a fridge for you? I haven’t even been paid yet,” Stiles’ shirt sleeves have been rolled up. A lot of the office had left already, the offices close at 5, no one really stays after. Except Derek. 

“No you idiot. Send an order to purchasing for a fridge. Something small to keep under your desk.” Derek didn’t mean to snap, he’s tired, and it’s only monday. 

“Okay. Second, I can’t leave. I’m only allowed to leave when you do. Part of my contract.” Stiles shrugs. 

Damn Laura. She knows Derek stays late into the night. She hired this kid to guilt him into leaving early. She’s good. 

“Well, I’m your boss, and I’m saying you can leave. I’ll probably be here until midnight and I don’t want to keep you here if you’re not going to be doing anything.” Derek pushes his plate for Stiles to take. He picks up the hint and takes the plate along with the utensils and water glass. 

“Ms. Hale said you’d say that. I’m still not allowed to leave until you do.” He stops for a second, “so, if you need me, I’ll be outside reading Star Wars fanfiction.” He walks out. 

It’s a whole thirty minutes before Derek gives in and starts packing files and folders into his briefcase and wraps up in his coat and scarf. He opens his door to find Stiles cheek in hand staring at a wall of text on the computer screen. 

“Are you really reading Star Wars fanfiction?” His presence must scare Stiles, because he jumps and inhales sharply. 

“Oh my god,” Stiles sits up straight in his chair and clutches his chest. “Where did you come from?” 

“My office. Were you wasting company time reading fanfiction?”

“No, I’m reading policies and procedures. I’ve been reading it all day because I have nothing better to do.” Stiles looks him up and down. “Are we leaving now?”

“Yes,” Derek doesn’t say anything else, just continues to walk past the desk and to the elevators. He hears Stiles behind him scramble to get his things together. He slides into the elevator just as the doors are starting to close. 

“Thanks for holding the elevator,” he says as he continues to put his coat on. The ride down in quiet, and Derek has a slight inclination to ask Stiles some questions. About what, he doesn’t know, but he just kinda really wants to talk to him. 

They reach the ground floor and Stiles bolts, “See you in the morning boss. I’ll have your coffee waiting!” Before he knows it, Stiles is out the door waving to the security guard at the desk near the exit. 

The elevator closes and jerks into motion to go to the underground parking garage. He tries to let go of the tiny budding feeling in the back of his head. The drive home is difficult, but traffic in the city is always difficult. 

He has to admit, being home and in bed by 10pm is kind of amazing. 

 

The next few months go in much the same routine. 

It’s about 6 months after Stiles started, and Derek has warmed up to Stiles a little. He’s a sarcastic asshole sometimes, but Derek has become so much more productive since he leaves work earlier and actually sleeps and eats now. 

The last thing he expected was to come out of his office for a quick restroom break to find Stiles at his desk on the phone. 

“Yeah, I think I’m gonna put my two weeks in. He’s such an ass. He keeps me here until 8 every night, and that isn’t even that bad considering I used to work at Jungle, but then I have to turn around and be here at 6am? It’s not worth it. Plus, did I mention he’s an ass?” He pauses, whomever he’s on the phone with responding, “Yeah dad, I know this is a good job. The health insurance is amazing, and I’ve never had this much money in my entire life but I don’t think that I can-”

Derek coughs.

Stiles turns around in the swivel chair to see Derek standing there with his arms crossed over his chest. 

“OhmygoddadIgottagobye. I’llcallyoulater. Loveyou. Bye.” then hangs up the phone. “How much did you hear?”

“Enough. You can start clearing out your desk,” Derek answers as he passes Stiles deskt to head to the bathroom. 

“Mr. Hale, I-”

“I don’t have the time or money to deal with people who don’t want to be here. If working here is some sort of inconvenience to you then you don’t have to work here. I’ll tell HR you gave me your two week, you can be done here as soon as you clean out your desk.”

“But sir I-” Stiles tries, Derek doesn’t let him finish, he walks away and keeps his sights on the restroom. He had no idea Stiles was so unhappy. If anything, he thought they were finally hitting their stride. He hears a soft ‘fuck’ from down the hall. 

When he comes back Stiles’ jacket is gone, but all his ridiculous little toys are still all over his desk. Derek wonders what it means, but goes back into his office to finish out the day. He emails Laura to hire him a new, better, assistant. 

Fifteen minutes after he sends the email to his sister, she shows up at his door. 

“What the hell Derek?” She barges in with no regard for him being on the phone and trying to hold up his finger to let her know to give him some time. “Don’t fucking do that Derek,” she swats its down. 

“I’m sorry Satomi, I need to call you back. Okay, yeah of course. Talk to you soon, okay, bye.” He puts the phone on the receiver. “What do you want Laura? I was talking to Sotomi!” 

“What happened to Stiles?”

“Mr. Stilinski, no longer wanted to work here.” Derek tries, but Laura knows him too well and stares him down. “Fine, I walked in on him talking to his dad on the phone complaining about wanting to quit. If you’re going to hire me an assistant find someone who wants to work here.” Derek is more than a little agitated. Stiles was the only assistant he was given that he liked, even if it was the most miniscule amount. 

“He wanted to work here, your last assistant Erica, is one of his best friends.” Laura puts her hands on his desk and leans over to stare at him in the face. “She told him the position was open, he applied. When I interviewed him, he was excited for an entry level position so he could work his way up. He has a degree in Computer Engineering and wants to work in the IT department,” she was yelling now, Laura rarely yells. “You scared away our next CIO.” 

This is serious. 

“Get. Him. Back.” She’s leaning in closer than anything Derek would ever be comfortable with. 

He swallowed, “okay.” It’s all he can say, his older sister always scared the living crap out of him. She turns on her heels and storms out of her office. From the door, Derek can see a few of the faces down the hall looking scared to have heard yelling from his office. 

Without another moment to spare, he pulls up Stiles’ employee file to try to get him back. How bad was it that he didn’t know his own assistants phone number? The number comes up and Derek punches in the numbers, it’s a California area code, he makes a note to ask Stiles where he’s from if he gets the chance. No answer comes, but Stiles voice comes when the voicemail answer comes, “Hey, you’ve reached Stiles. Do your thaaang,” then a beep. 

“Stiles, this is uhh- Derek. Hale. Derek Hale, your boss. I would really appreciate it if you came back to the office. There are some matters I would like to.. discuss with you.” Derek doesn’t really know what else to say, he barely knows the kid. “Also, you left your toys here, I’m going to throw them away if you don’t retrieve them by the end of the week,” he hangs up. 

As soon as he does he feels like he fucked up. The idea of calling him back and leaving another message gives him anxiety. Geez you would think he’s texting a middle school crush rather than asking for a meeting with his assistant. 

Stiles doesn’t come back for the rest of the day, Derek orders a box from human resources to put all of Stiles’ toys in to make room for the new assistant who should be coming any day now. He’s a little sad that he won’t see Stiles anymore.

The next morning, he somehow sleeps through his alarm and wakes up when the sun is streaming into through the blinds. 

“Fuck,” he says as he rushes to get ready. Deciding he doesn’t have time for a shower, he tosses on a suit and rushes out, briefcase in hand. Traffic looks bad, so he decides to take the subway, which isn’t ideal, but he’s 4 hours late, the company may just be exploding without him. 

It’s nearly eleven when he pushes through the people in the elevator to get to his office. 

“Sorry, excuse me,” the people just didn’t seem to want to move out of his way. When the people finally wiggle enough to make room for him to exit he speed walks past the girl at the big front desk where Hale & Co. is lit up behind it.

“Good morning Mr. Hale,” says the girl, he doesn't know her name. 

The walk to his office seems longer than normal, all the eyes of his employees watching him as he passes all of their desks. This is probably the first time many of them have seen him.

He turns the corner to the hall where his office is, expecting the desk outside his door to be empty. Instead…

“Hale & Co. One moment please. Hale & Co. Please hold. Sorry for that little wait, what can I do for you?” Stiles is sitting behind the desk, phone nudged between his shoulder and ear as he logs the call on the computer. “Nice to hear from you again Mrs. Gregerson. Mr. Hale is actually out of the office at the moment, but I will tell him to call you back as soon as he gets in.” he’s quiet as Mrs. Gregerson responds, then lets out a laugh followed by, “Well, Mrs. Gregerson, you tell your son that I will see him at the bar and we’ll see what happens,” another laugh, “Fine,” he grabs a pen and a sticky note and jots something down. “I’ll give him a call. I need to get back to answering phones Mrs. Gregerson, nice to talk to you. Bye.” Then hangs up. 

He goes to push the button to answer a call on hold, but Derek is just standing there, shocked that Stiles is even there.Stiles notices him. Since he woke up late, he’s wearing his glasses and his beard is a fuzzy mess. Stiles though,he’s wearing his contacts today, he looks good. 

“Where the hell have you been? The phone is ringing off the hook.” Stiles turns the monitor to show the call log.

“I woke up late,” Derek puts his head down and walks into his office. 

It’s a good couple of hours before he catches up with all the calls he missed. Derek makes a plan to set a few extra alarms from now on, the company would fall apart without him. 

He’s so wrapped up in his work and answering phone calls that he when his stomach growls in a loud protest he’s taken aback. As if by magic, Stiles swings the door open and puts a steak down on his desk. 

“Your lunch sir. Sorry it’s a little late, the phone didn’t stop ringing until after 12.” Stiles steps away and puts his hands behind his back. Derek looks as the clock and sees its nearly 2pm. “Then there was an accident on 78th street so I couldn’t get a salad for you, I hope the steak is good. Also, where are all my action figures?”

Derek pulls the tray of food closer to him and takes his tie off so it doesn’t drip into his food. 

“Your dolls are over there,” he uses the fork to motion to the corner of his office where the box is sitting next to the couch. “You’re lucky I didn’t throw them away. After you left like you did.”

Stiles doesn’t say anything. Derek was expecting a witty comeback and some sort of snarky comment about how they’re not dolls, but action figures. They’ve had the discussion about the difference between the two many times before. It was one of his favorites. 

Instead, Stiles walks over to the box, picks it up, and walks back towards the door without another word. 

“Actually,” Derek can’t stop himself from saying, “would you have a seat, Stiles?” He has a piece of steak stabbed on the end of his fork when he uses it to point to the chairs in front of his desk. They rarely saw any action, considering Derek never had to entertain guests in his office, that is Laura’s job. “There is something I wish to discuss with you.”

In all the time he’s worked with Stiles, he’s never been so hard to read as right now. With the box in his hands, he looks sad and pathetic, like he is going to be canned any second now. He also looks like he knows it’s coming, an official end to yesterday’s incident. He takes a seat and keeps the box on his lap. 

“Why did you come back today?” Derek shoves the meat into his mouth, making it clear that Stiles will be talking for a bit. 

“It’s my job to be here at 6am, and leave when you do.”

“That’s a very different attitude than you had yesterday,” Derek takes a swig of water, he wonders if Stiles had food on his desk getting cold while they talked. 

“I wasn’t feeling well yesterday, I didn’t want to be at work. I would have rather been at home with my dad,” Stiles adjusts his seating. 

“Why didn’t you ask for the day off? Call in sick?”Derek asks. 

“My dad lives in California, and if I wanted to visit him I would probably need a week off. I don’t want to ask for that much time off still being new to the company.” Stiles is being serious. More serious than Derek has ever seen him, there is something in his eyes that is making Derek feel bad for even suggesting that Stiles didn’t want to be here. 

“What’s so important about this week that you would need it off?”

“I’m sorry sir, but that isn’t really your business. You need to be a level 5 friend or level 2 romantic interest to unlock my backstory,” he finally cracks a smile.  

Derek puts his fork and knife down, “Why did you apply for this job?”

“I live for getting coffee and lunch for people. It’s my passion, I can’t imagine doing anything else except get you coffee and redirect your phone calls for the rest of my life,” Stiles puts the box with his dolls on the floor, deciding he’s going to be here for a while. 

Derek just deadpans him. 

“Hale & Co has a top tier technology department, one of the best in the world, I just wanna work with them. You only hire people with connections and since I have none, the only way to get my foot in the door was to put up with you until a job opened up, then hoped that you would let me give it a shot.” Stiles slinks into the chair like this was suddenly between two friends rather than a boss and an employee. Why did Derek hope it was between friends?

“That’s why you came back,”  Derek says, looking down at his desk. In the farthest part of his brain he kind of hoped Stiles came back for him, but he wants a job with the company. He tries to not let the tiny freckle of hurt show. 

“Yeah,” Stiles says, his brown eyes down cast to his lap where his hands were joined together. “I’ve been out of college for 3 years, and I need a grown up job. Bloos was nice, it was my baby, but it wasn’t what I was passionate about. So I left my stable job serving coffee to come and be your assistant,” he takes a breath and brings his hand up to rub between his eyes. “And I messed that up too.”

Stiles looks so sad, like maybe he really thought this was going to pan out, but he didn’t realize how much of a handful he was. Erica quit after three days. Stiles has lasted the longest out of all his previous assistants. He needed to fix this.  

“Laura emailed me your contract,” Derek starts, then moves to grab the mouse and open his email. “I read it over, and if you’re available, I would like to maybe modify it a little.” Derek swivels the computer screen to show a pdf of Stiles contract. 

“Ummm…” Stiles is looking at him like he grew a second head. “Why??” He draws it out for a few seconds. 

“When you left, I realized you’re the best assistant I’ve ever had. Laura came and gave me an earful about you and I didn’t even look at your resume when you started. I didn’t think I needed too. But since my sister is insistent, I looked at your resume last night. That’s why I woke up late today,” Derek rubs his eyes, a bit of sleep sand comes out. 

“Okay?” Stiles is not sitting sprawled in the chair, gripping the arms like he’s going to float off into space if he lets go. 

“I’m willing to make some compromises, but that would require you to work harder than you have been in the past few months,” Derek commands the pdf to print and the printer behind him groans to life as the contract is printed. 

“Why are you doing this?” 

“Because, you resume is very impressive for someone applying to be an assistant. Too impressive,” Derek turns around and grabs the papers warm out of the printer. “There is an internship opening up in the IT department this week, and considering your background in computer science, I think you would do well in the position. It’s unpaid of course, so you’re welcome to continue being my assistant, but the choice is yours.” Derek pauses for what he hopes is dramatic effect, “So would you like to renegotiate?”

Stiles just nods furiously, sticking his tongue out in the process. Derek finds it adorable, and forces himself to focus on the new contract they’re going to build together. 

 

Stiles leaves thrilled. Derek would be too with all the new things in his contract.

It wasn’t that hard, Stiles agreed to staying on as Derek’s assistant, which he was silently thrilled about. Stiles made his concerns about arriving early and leaving late clear the day before, so added in the contract was that Stiles was to arrive at 8am and leave no later than 6, to which Derek agreed to abide by the hours as well. 

It surprised Derek how much Stiles seemed to care about him. When it came up that Stiles was going to be getting to work at 8 instead of 6, he asked if Derek would follow that too. Claiming, “you need to take care of yourself too. I know you’re a big shot here, but you need to sleep some time.” Derek couldn’t say no to that. 

In addition to the time as Derek’s assistant, he could spend 4 hours down in IT. Working with them, most likely getting coffee and lunch, but he still seemed thrilled. 

“I told you getting coffee and lunch was my passion!” Stiles exclaims when they get Jim from IT on the phone to okay the internship candidate. If Derek emailed him late last night about the creation of said internship, no one needed to know. 

It’s all worth it though, when Stiles signs the new contracts and picks his box of dolls up and practically bounces out of the room. 

“Thanks Mr. Hale,” he pops his head back in when the glass door starts to close. 

“Call me Derek,” he responds before he really thinks about it. Why did he do that. Why did he do that?!

“Okay,  _ Derek,” _ Stiles shoots back and the smile on his face is electrifying. Derek gruffs and goes back to his steak, which is now cold. Oh well. 

 

Stiles starts thriving. He spends most of his day sitting at the desk outside of Derek’s office, but if he’s not there he’s down in the IT department, getting coffee orders, or shadowing someone to fix computers. 

He always comes in to give Derek his lunch complaining that he knows all the things they’re teaching him, and Derek will shoot off an email to Jim asking him to find Stiles something more lucrative to do. Jim starts having Stiles look into firewalls and other things he doesn’t quite understand. 

Stiles is thrilled though. That’s all Derek can really ask for. 

Seeing Stiles with a skip in his step when he comes in with coffee and the smile he has after his leave in the IT department makes Derek’s heart soar. 

True to his work, Derek doesn’t show up until 6 am, and he leaves with Stiles every night. With the water Stiles keeps under his desk, his work productivity actually increases. Laura calls him bragging about the excellent choice she made in adding Stiles to the team. Derek agrees, not to her face, but the company really would be a lot different without him. 

The other employees are even doing better, he’s a sarcastic ray of sunshine. He’s an asset he’s glad he didn’t let them slip away. 

Its another couple months that Derek notices how hard he is falling. Every time Stiles enters his office, Derek’s heart flutters, and if Stiles wears his glasses and a beanie his pants get a little tight. He’s gone on his assistant, and there is nothing he can do about. 

He puts it off though, shoving it back into the deep corners of his mind. He does have a company to run after all. The Gigatti’s want to have a conference call, one that because of time differences will take place at nearly 2am in New York. The call can’t be made from the comfort of his condo, so he’s going to need to stay late. 

Considering he hasn’t been at the office alone for a few months, the thought of staying all night alone makes him uneasy. He knows he promised Stiles no more late nights, but he has to at least ask, right?

“Stiles, can you come in here for a second?” Derek calls over the phone. Without a response, Derek hangs up. A few seconds later, Stiles walks into the office, like he has hundreds of times. He’s got a Fresh-Out-Of-College vibe going today. His usual khaki pants were changed out for a pair of tight jeans, and he has on Converse instead of the usual Oxfords. His shirt is white and crisp, you can see his undershirt though it. The sleeves are rolled up to his elbow exposed the veins that are popping out of his forearm, Derek has to work really hard at hiding the arousal from just the sight of them. 

His whole look today makes Derek work really hard to keep the idea of grabbing his ridiculous skinny black tie and bending him over his desk right now. He doesn’t even know if Stiles is into guys, the only time he hear of Stiles possibly going on a date was when he was on the phone with Mrs. Gregerson, but damn, Derek’s kind of wants a piece of him. 

“What can I do for you Derek?” Stiles sets his hands behind his back.

“The Gigatti’s want a conference call at 10am tomorrow,” Derek starts.

“Okay, cool, I’ll send a request for a conference room, how many people are we expecting? Should I cancel your 10:30 with Dr. and Mr. Stronghold?” Stiles starts to ramble off. 

“Actually, the conference is going to be a video call at 10am Central European time, so 2am for us,” Derek is nervous, and he really shouldn’t be. Stiles is his assistant, he should not be having these types of feels for his assistant. 

“Sooo?” One of Stiles’ eyebrows goes up while the other scrunches down, it shouldn’t be so damn cute. 

“We’re going to need to stay late tonight,” Derek finds himself twiddling his thumbs, trying to distract himself. 

“Umm, I kind of have a date tonight…” Stiles starts, one hand comes up to his head to flatten out the back of his hair. 

“Oh um,” Derek didn’t expect that, but it was Friday. “It’s fine, I’ll ask someone else to stay with me.” He looks away, back towards his computer screen. 

“I can cancel, I only agreed to go out with him because Mrs. Gregerson was insistent. Her son is about as interesting as white paint,” he huffs out a laugh. 

“No, I’m sure Laura would rather be here,” Derek leans over to grab his phone to call her, anything to distract him from the embarrassment he’s feeling on his cheeks. 

“Please, I’ve been looking for an excuse to get out of it. Plus, you’ll be lost without me, In case you don’t remember, I’m an intern in the IT department. You need me,” he smiles and straightens his tie even though it doesn’t need it. “Plus plus, I know where all the good chinese take out is,” and how can Derek say no to that?

“Fine, but only if you’re sure.” Derek is a little sceptical that Stiles would so willingly ditch his date to be bored in the office until 2 am. 

“Positive,” Stiles nods resulutely. 

“Great,” is all Derek says. Tearing his eyes away from Stiles to look back at his computer screen. 

Stiles leaves the room while also announcing that since the morning calls are all done, he’s going to head down to the IT department and hang out there for a little bit. Derek grunts in response and does not watch Stiles walk out. Nope. 

At 5 o’clock Stiles pops back into his office, smelling mildly of weed and a way to much body spray. 

“So, I called Mitchell, told him about tonight. He said that 10 am in Rome is 4am here, not 2am.” He looks like he’s getting ready to be called a name or something, which to Derek’s credit he has never done… as far as he remembers. 

“Oh,” Derek thinks about it for a second to realize that Stiles is right, how did he make a mistake like that? “Yeah, it slipped my mind.” Derek thinks for a moment while Stiles stands in front of him waiting for something to do. 

4am is way too long for someone to stay at work, even by his standards. Then getting in the next day will be hard too. Plus, Stiles has a date and even though Derek isn’t jealous at all, he has been doing a good job and deserves to have fun. That kind of settles it. 

“Since that is late, you can leave as usual. I’ll leave as well, we’ll get here at 3, setup, and have the meeting then instead of waiting for it to come. That way you can still go on your date, and we can get out of the office for a little while,” he finds himself nodding resolutely, because it is a smarter plan than staying at the office until the meeting. 

“Really?” Stiles face seems to light up. 

“Yes. Then if it’s okay with you, we can stay at work after the conference. Since it’s Friday, I’ll let you leave at noon, for coming in early.” It’s only fair. 

“Dang, Derek. When did you become the cool boss?” Stiles mouth quirks up in a half smile, making a little dimple on the side of his cheek. 

_ Stiles thinks you’re cool _ , plays over and over in his head as Stiles throws a thanks over his shoulder, claiming he’s going to call this Mitchell guy. 

As promised, Derek and Stiles walk out of the office together. Their shared ride down the empty elevator is filled with Stiles’ usual chatter of what he did with the IT guys. Derek only understands about half of it, but he loves hearing Stiles talk, he gets really enthusiastic and starts waving his hands around. It’s endearing. 

“Well Derek, I’ll see you in a bit!” Stiles adjusts his bag on his shoulder. There is a Mercedes Benz sitting at the curb, it’s lights are on. Stiles must see Derek noticing because he says, “That’s Mitchell, Mrs. Gregerson's son, I told you about him. The car is nice but I think he might be overcompensating for something.I don’t know though, we’ll see,” he winks and turns to and walks to the revolving door. 

Mrs. Gregerson is one of Derek’s favorite clients, but he’s never met her son. Suddenly Derek’s stomach starts to turn. There is no logical reason for Derek to be jealous of this Mitchell guy, but that can’t explain the feeling bubbling up in his mind. The thought of Stiles in bed with someone who wasn’t him makes Derek’s little green monster grow in size. 

Stiles’ “we’ll see,” rings in his head as he unlocks his Camaro and leaves the parking lot. 

Usually, Derek is too tired after work to do much else, but the tightness in his stomach is making him antsy and he really just wants to blow off some steam, and seemingly without notice he finds himself at the gym a few blocks away from his condo. 

The gym is empty. Everyone is on their way home on a Thursday, not at the gym. 

Derek works out for longer than he’s used to, and he knows he’ll be sore in the morning. He didn’t realize how long it’s been since he’s been to the gym. 

Two hours after he arrived he decides he’s done, his legs are trembling a little, and he’s grateful his condo has elevators, otherwise he’d be sleeping in his car tonight. The streets were just as crowded now as ever, gotta love the city. 

The hot shower that is waiting for him is amazing and it’s even more amazing slipping into the fresh cool sheets the housekeeper changed earlier that day. Before he drifts off completely he sets his alarm for 2 and slips into sleep. 

Dreaming is an uncommon occurrence for Derek. He’s often too stressed to dream, or if he does dream they’re flashbacks to the fire, nightmares more than dreams. So when Derek has visions of Stiles laying in bed with him, and standing in his kitchen wearing boxers that were obviously too big on him, leaving soft kisses on Derek’s lips, Derek is startled awake. 

The clock says it’s 1, since he needs to be up in an hour anyway, he swings his legs over the edge of his bed, feeling some tightness in his legs, while trying to grasp small parts of his dream. Small whips of what could be to save for later. 

He plops himself in front of the tv and pulls out some dispositions from his briefcase and starts reading through them as the tv buzzes with static electricity and late night talk show reruns. The Gigatti proposal finds it’s way out of his briefcase, and before he knows it, he is making changes and adjustments he thinks they will really like. Before he knows it, his phone is coming alive to the soft sound of an old phone ringing. Derek pushes himself off of the couch and goes to get dressed. 

The city is peaceful in the early hours of the morning, it’s one of the things he misses most about being at the office before everyone else. The streets only occupants are late night taxis, and a few town cars, cyclists getting in their morning ride, even a few skateboards pass him on his way to his building. 

Derek pulls up to the entrance for parking just as soon as the same Mercedes pulls up at the front of the building. He suppresses the jealousy as he watches Stiles pop out of the car in the same clothes he was wearing the last time they saw each other. 

The metal gate arm rises for Derek to go in, his car lurches forward just in time to avoid Stiles ducking his head back into the Mercedes. 

Derek takes the elevator up, not seeing Stiles or the car as he passes the first floor. He decides to call Stiles, so he pulls out his phone and hits his contact (which is Aa Stiles so it’s at the top of his contacts list. Ya know, for emergencies). 

“‘Morning boss,” Stiles answers. 

“Are you at the office?” 

“Yes sir, I am. Just got here. I’ll be up in a second. The subway was a bitch this morning,” his answer makes it seem that he didn’t see Derek pull in at the same time he did. Derek doesn’t know what it means that his chest stings a little bit with the lie. 

“I’ll be in my office. Get conference room c for the call.”

“Got it, see you soon.” He hangs up without saying a goodbye. 

His office is quiet and dark, the floor is clean, and the windows are sparkling with the lights of the city. Derek adjusts his tie and sits at his desk so he can prepare for the meeting more fully. 

A few moments later, Stiles figure shows through the glass door. His head pops in a few seconds later. 

“Hey there, the conference room is all set up,” he walks into the room and he’s wearing new clothes now. He must have changed as soon as he got in the office. “You want coffee now or do you want to wait?” His hands are shoved into his pant pockets. 

“Just make what we have here, it’s fine,” Derek answers. Without further instruction, Stiles leaves the room to get coffee from the small communal kitchen. Derek takes the moment to breath, he’s got about half an hour before the meeting, and suddenly he’s nervous. Maybe he should have asked Laura to help him.

He’s lost in thought, in worry, when the paper cup is put on his desk, Stiles sits in a chair across from him with his own cup. 

“Did  you have sweet dreams boss?” Stiles questions, Derek grunts and picks up his files and the coffee. 

“Let’s go,” Derek is almost at the door, Stiles springs up and goes to open the door for him, then follows him out. 

Conference room C is a small one, fit for about 6 people, Derek sits right across from the computer that is set up. Stiles tinkers with it for a few seconds, then the thing comes to life and the company logo is on the screen, waiting for the other party to join the call. Derek notices Stiles pull out a notepad and take a seat next to him. 

The screen comes to life with a group of men and women and the meeting begins. 

Derek goes over the changes he added to the contract and they discuss the plan a few more times before Derek instructs Stiles to fax them the contract. Within the hour, the contract is back in their hands, signed and dated. Goodbyes were said and the deal is done. The tension from his shoulders finally drops as Stiles shuts off the call. 

“Nice job Boss! I got your notes here for you, do you want me to type them up?” Stiles holds up the notepad.

“No, don’t worry about it. Hey how was your date?” the two men walk alongside each other back to Derek’s office. 

“Oh,” Stiles sounds surprised that he remembered. “I think misjudged him earlier, he seems really great.” The smile on his face is hard to miss, but Derek pretends he doesn’t notice. 

“Thats nice,” he has no idea how to continue this conversation. “Where did you guys go?”

Again, Stiles eyes seemed surprised that Derek is making any sort of conversation. He has every right to be, after all, Derek hasn’t been any friendlier towards him, even after the contract renegotiation. 

“We uh, we went to this really nice place that I was way to underdressed for. We ate, had a few drinks, then he took me home. It was nice,” Derek can tell that Stiles is at least a little bit smitten with the guy. 

“That’s great, I hope you guys uh, keep going.”  _ Why would you say that? _ He asks himself.

“Yeah me too,” the reach his office and instead of Stiles taking a seat at his desk he follows Derek inside and sits, in what looks like a very uncomfortable position, on the chair he had earlier. 

They sit in silence for a few minutes, but it’s interrupted with Stiles question “Why do you work so hard? Like, I know this is your company, and yadda yadda, but, you have a staff of over 400 people, but yet, you are the one doing everything. Why?”

Derek looks at him and raises his eyebrows. 

“I mean, it’s totally not my place, but ever since I started working for you, i’ve noticed that you work ten times harder than anyone else here. I think you work harder than Laura.” Stiles words lose confidence as he goes on with his sentence. It leaves them in silence again, but the comfort in it is gone, and it’s a little tense. 

“This is my parent’s company. They built everything you see,” He stops, because just the thought of them makes his throat constrict a little bit. “When I was in school, I dated someone. They didn’t approve of her, and I didn’t listen. I thought I was going to marry her, and my parents gave me an ultimatum. I can marry her and be disowned, or I could leave her and stay. I left, and when she found out that I wasn’t going to have any money, she left me. She left me and set my parents house on fire,” a hot tear falls down his cheek. “They died because of me. So now, I have to make sure that they didn’t die in vain.

“I work harder than anyone here because if I fail, if I let this company fail, then I’ll be the disappointment my parents know I am.” Derek doesn't know why he said all that, but Stiles has been around for long enough, it’ll be a year soon. Stiles is probably the closest thing he has to a friend. 

“Oh, well, that explains it then,” Stiles is quiet for a second, then continues, “I'm sorry about your parents, my mom died when I was ten so I kind of get that.” They’re quiet for a beat more, “Remember when I almost quit?”

Derek nods.

“Well, that was her anniversary. I don’t really remember much of her, just a few things here and there, but my dad is a wreck every year. This is the first year I wasn’t really able to be there with him,” Stiles takes a sip from his coffee. “He’s an alcoholic, and he’s sober 99% of the year, and every year we try to get through it without him drinking, but it’s hard on him. This year he really wanted his one year chip, but I couldn’t be there.”

Silence fills the room again, Derek feels intimately close with Stiles in a way he hasn’t been before. 

“Where is home for you?” Derek asks suddenly, a plan concocting itself in his mind. 

“Beacon Hills, it’s a tiny town in Northern California,” Stiles swirls his cup, mixing up the contents. 

“I grew up there, well, my parents grew up there, they had a house out there to escape the New York winters. It’s a nice little town,” Stiles laughs at that for some reason, but doesn't respond. “You can have that week off,” Derek starts, but then hastily adds “if you need.”

“Wow, really?” Stiles changes how he’s sitting. 

“Of course, Beacon Hills is a long way to be away from your dad. Family is important. The company will go on without you I’m sure,” Derek laughs lightly. 

“It’s still a good while away, let’s see if you can keep me here that long,” they sit and talk for a little while longer, the sun rises outside and the reflection off of the buildings stream into the office. They talk about a lot of things, and Derek can’t really believe how easy it is to talk to Stiles. The thought only makes it hurt more when he remembers Stiles is dating someone else, and that he’s his assistant. 

They aren’t torn away from their conversation until the phone on Stiles’ desk starts ringing, and it’s hard to believe that it’s already 8am. Derek can see other workers are fluttering into the office when Stiles opens the door to go back to his duties as the assistant. 

After that morning, Stiles and Derek create a sort of friendship, Stiles doesn’t buy lunch when he buys Derek’s lunch, instead he brings his own. They start eating lunch together in Derek’s office, Stiles talking Derek’s ear off about the gossip amongst the cubicles. 

A comfortable routine forms between them, when Stiles has the time. 

Micheal from the IT department quit unexpectedly, and with the shortage, Stiles was called to help until they can hire someone else. Which means Derek ends up having to answer his own for sometimes. Not that he minds until...

“Hale,” he answers the call. 

“Ummm, hello?” the voice answers. 

“Hello, this is Derek Hale, who is this?” Derek barks back. 

“Is um, is Stiles there?” the voice asks, and it throws Derek off. Who would be calling Stiles. 

“Who is this?”

“Mitchell Gregerson, his boyfriend?” Derek wants to groans, why is he calling the office phone to talk to Stiles? “Where’s Stiles?”

“Mr. Stilinski is assisting in an office emergency. There are no personal calls during business hours. Don’t call this number again.” He hangs up. 

Boyfriend? They were officially boyfriends? Derek puts it out of his mind, and dials the number to the IT offices. 

“IT. This is Roger,” the guy- Roger- answers the phone. 

“Is Stiles there?” Derek asks, his voice is gruff, and he knows it. 

“He is, may I ask who’s calling? He’s dealing with a bit of a crisis, but I’ll send him up- ” 

“Derek Hale.” Roger is too cheery for the situation so Derek interrupts. “Send him to my office right now.” 

“Oh,” at the sound of his name, Roger gets with the program. “Yes, I’ll send him right away.” Derek hangs up again. 

He doesn't really know what he’s upset about, personal calls weren’t allowed but it was fine every once and awhile. He’s not angry that Stiles isn’t here to answer his phone, he did it on occasion when Stiles helps out downstairs. There isn’t much time to think before Stiles bruts in through the glass door. 

“Roger said you were pissed, what happened?” He’s out of breath like he ran all the way here. 

“Your boyfriend called,” Stiles keeps typing what he’s typing. Well, he keeps pretending to type something. 

“My boyfrie- Mitchell? He’s not my boyfriend,” Stiles plops down in the chair. 

“Then you might want to tell him that,” Derek keeps typing and hopes that Stiles doesn't notice him typing the same sentence over and over again. 

“I stopped seeing him,” Stiles admits. “Or rather, I told him last night I didn’t want to see him anymore. There’s someone else...” Stiles doesn’t finish his sentence. 

“Well, whomever it is, there are no personal calls during work hours. So you’ll have to call them on your own time.” Derek stops typing to look at Stiles.

“Okay, I’ll tell him not to call unless it’s a business matter. Is that all? They still need me down there and-” Stiles starts to shift in his seat, about to stand up. 

“Actually, in regards to that, you’re fired.” Derek says off handedly. Jim called yesterday asking if they could hired Stiles to replace Micheal. 

“What? You can’t just fire me for Mitchell calling me on company time! That’s unfair and I’ll sue!” Stiles pushes himself out of the hair and sets his hands on Derek’s desk. Leaning over it to get more in his face.

“Why would you sue the company you’re working for? That seems like a little bit of a conflict of interest.” Derek sits back in his chair, trying to stay out of Stiles’ personal space.

“You just fired me dumbass,” his eyebrow cocks up, and he looks at Derek like he’s an idiot. Derek thinks he sees what’s going on here.

“Jim didn’t talk to you?” The wheels on his chair allow him to pull farther away from Stiles. 

“Well Jim was talking to me before you had Roger barge in telling me you were pissed. I can’t believe you called me in here to yell at me about my ex and fire me!” Stiles has one hand on his hip and the other is carding through his hair as he starts to pace a little in the small space of Derek’s office. 

“What? No Stiles-” Derek has no idea how to handle this situation. 

“You know what Derek? Fuck you. I thought we were getting to a place where we could-” he stops and tightens his lips like he can’t say what he wants. “I’ve been dealing with your moody ass for almost a year and this is what I get? Fired because my ex called me at work?” He pauses again and Derek can see genuine hurt on his face, he needs to say something before it’s too late. 

“Stiles Jim was going to-”

“Jim?! Jim was going to fire me? Great. No one will hire me when they see I got fired from Hale & Co. Fuck.” Stiles chest starts heaving and his face gets flushed. Derek is a little scared he might have a panic attack. He remembers Stiles telling them he gets them sometimes a few weeks ago over lunch.

“You’re not fired!” Derek yells just as Stiles plots down into a chair and loosens his tie to get more air in his lungs. 

“What?” Stiles is out of breath even though he hasn’t done anything to warrant it, his face is flushed still and Derek is still a little scared he’s going to have an attack anyway. 

He stands up and moves to sit with Stiles in the chair next to his. 

“I guess I pulled you away right when he was going to offer you the job but I took you away before he could finish,” Derek starts, Stiles has his head in his hands, leaning over trying to calm down. 

“What job offer?” he says, a breath between each word.

“Well, since Micheal left, Jim needs to replace him, and since you’ve been doing better than anyone expected he was going to offer you the position.” Derek pauses and Stiles looks up at him, “I was going to fire you so that you could move there full time. “ 

“Are you shitting me? I can’t take anymore of this emotional rollercoaster you have me on,” Derek has no idea what that means. 

“No, I’m not messing with you. You’re going to finish out the week with me but starting next week you’ll be moving permanently to IT.” Derek says cautiously, he still can’t tell what Stiles is thinking. 

“So, I’m being promoted?” Stiles face light up, still tinted red at the cheeks and ears.

“In a way, yes,” he answers. 

“Holy shit,” Stiles says, face falling. “Holy shit!” he jumps up and fist pumps the air. He looks amazing in this moment. His amazing brown eyes light up and he’s smiling so big Derek wonders why he  doesn’t smile like that all the time. “I need to call my dad! I need to call Lydia!” Derek has no idea who this, Lydia, person is. Maybe the ‘someone else’ Stiles mentioned earlier, and it kills his mood.

A bud of jealously blooms in the back of his mind again. He kind of hates that it’s shown up.

Stiles continues to celebrate his new job. Ridiculously jumping up and down, and giving himself high fives. It would probably make his heart flutter but he’s too busy thinking about this Lydia person. Then he suddenly stops and turns to look at Derek.

“Wait, so after, this week you won’t be my boss anymore?” His eyebrows quirk up, as well as the side of his mouth. It’s a devious look, and Derek has no idea what that means. 

“Well not directly no. I still run this company under Laura, but-”

“But you won’t be my direct supervisor?” Stiles finishes. 

“No, I suppose not.” He has no idea what Stiles is thinking, but it puts a smile on his face that is different than the one he had a few moments ago. 

“Great,” his smile is still there.

“Don’t sound so excited,” this whole thing is confusing him. “Get back to IT, before they fire you too.” Derek stands up and moves back to his side of the desk. Stiles nods once, and turns to leave his office. 

Fuck his ass looks good in those pants. 

 

The rest of the week goes as good as it can, Stiles starts spending more time in IT than outside of Derek’s office, Laura already has a new assistant out there by Friday morning. All his toys are gone by the time the new girl starts. That day, Stiles last day as  his assistant, he doesn't even see him. 

The thought of only seeing Stiles in meetings or when his computer acts up makes him upset. Mostly because he’s grown very dependant on Stiles, not only as his assistant, but as his main social entertainment. Which isn’t saying much, but the new girl at the desk is terrified of him in a way Stiles never was. 

He’s gonna miss that. This new girl, Anna, comes when he whistles at her. He won’t keep it up, but he remembers how Stiles did not accept that. The memory puts a smile on his face as the clock says it’s quitting time. 

Monday Morning comes, and Anna puts his coffee down without saying a word. The one sugar he asked for tastes wrong on his tongue it must be the two sugars Stiles got him used to. He’ll need to ask Anna for two sugars. 

The office starts to come to life as it normally does. Derek goes about his normal business and readies himself for a meeting with some new clients in a about an hour. 

The phone rings. 

“Mr. Hale, there’s Mr. Stilinski here to see you?” Anna’s voice sounds pitchy, like she’s trying hard to keep it steady. The mention of Stiles floods his brain with what he can only explain as a bunch of exclamation marks.

“Send him in,” he manages to keep his own voice steady. Derek for a moment has a panic over if he should stand or stay sitting, but ultimately decides sitting is best just as the glass door swings open. 

“-gets better. I promise, he’s not that mean. Also, it’s two sugars even though he asks for one,” he’s calling out to Anna as he’s walking backwards into the office. He’s wearing black pants and a white short sleeve button down shirt. “Derek!” he turns to face Derek. 

He’s got on a black tie, and his employee ID is in a pocket protector?

“If I’m going to be in the Nerd Herd, I need to dress like I’m in the Nerd Herd,” he says as he raises his arms and turns so Derek can get a 360 degree look. Now he’s just being mean. 

“I don’t understand,” Derek admits as he stands and puts his hand out to shake Stiles hand. 

Stiles grabs the hand offered to him, “of course you haven’t seen Chuck, missing out man,” Stiles is casual, like he always is. Stiles doesn’t let go of his hand.

Derek sighs because he doesn’t have time to sit and watch television. “What do you want Stiles?”

“To do this,” where their hands are joined, Stiles pulls Derek over his desk and puts his hand on the back of his neck. Before Derek can fully comprehend what is happening, Stiles lips are on his. 

It’s- magical. Not that Derek believes in such things, but but there is no other way to describe what is happening right now. 

This scenario never played out in his head, it never really could. Stiles was his assistant. There could be nothing more than a strictly professional relationship. Now though, now he wasn’t Stiles’ direct superior. Jim is. Derek leans into the kiss and opens his mouth when Stiles asks for entrance. 

It takes them a couple of moments to get to the same side of the desk, but as soon as they do, Derek drags his hands up and down his back and finally gets to squeeze his ass. Derek can feel Stiles hard against his leg,and he’s sure Stiles can feel him. 

“Wait,” he stops himself. “What about Lydia?” Stiles new flame wouldn’t be happy about this.

“What about Lydia?” Stiles tilts his head that reminds Derek of a dog when it’s confused. 

“Won’t she get mad?”

“Why would she?” Stiles pulls back a little and the motion makes Derek a little sad. 

“Well, he’s your boyfriend. Unless you have an open relationship, which is cool but I don’t think I-”

“Ew no! Lydia’s my best friend and the closest thing I have to a sister. Ew no dude.” Stiles slaps his hand on Derek’s bicep, not enough to hurt but enough to get him to stop talking. “She knows my pining, she knows the struggle of keeping it in my pants. She’s rooting for this,” as if to put a stop to the discussion about his best friend, Stiles leans in again and kisses Derek. 

Derek doesn’t stop him. 

“Will you go on a date with me?” Stiles says as they break the kiss for a second to breath properly. 

“Fuck yes,” Derek goes in for another kiss. 

He never wants this moment to end. Ever. 

The phone rings. 

“What?” Derek answers it. 

“Jim needs Mr. Stilinski back in their offices.” Anna still sounds petrified to say the wrong thing. 

“I’ll send him down,” he hands up. “Jim needs you.”

“Okay, but I brought lunch, and I’ll tell Anna where to get your steak. I’ll eat up here today.” Stiles winks and straightens his tie. Derek rolls his eyes when he sees Stiles wearing Converse. 

“You better wear something more professional tomorrow,” Derek says as the glass door opens. 

“Sure thing, babe,” he winks again and Derek’s dick twitches. 

This is going to be interesting. 

**Author's Note:**

> So? What did you think? Leave a comment and a kudos to let me know! If there are any mistakes I'll fix em if you tell me. 
> 
> Did I miss something in the tags? Let me know!
> 
> Come hang out with me on [ tumblr!!](http://smokesforsterek.tumblr.com/)


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